Fungicidal triazolopyrimidines, method for the production thereof, use thereof for controlling harmful fungl, and agents containing said fungicadal triazolopyrimidines

ABSTRACT

Triazolopyrimidines of the formula I  
                 
where the index and the substituents are as defined below: 
     R 1  is C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 2 -C 10 -alkynyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 -cycloalkenyl, phenyl, naphthyl, or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon to the triazolopyrimidine and contains one to four heteroatoms from the group consisting of N, O and S;    R 2  is C 1 -C 4 -alkyl which may be substituted by halogen, cyano, nitro or C 1 -C 2 -alkoxy; n is 0 or an integer from 1 to 4; R is as defined in the description;    X is SO m —R x , NR x R y  or NR x —(C═O)—R y ; m is 0 or an integer from 1 to 3; and processes for preparing these compounds, compositions comprising them and their use for controlling harmful fungi are described.

The present invention relates to triazolopyrimidines of the formula I

where the index and the substituents are as defined below:

-   -   R¹ is C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,        C₃-C₁₀-cycloalkyl, C₃-C₁₀-cycloalkenyl, phenyl, naphthyl or a        five- to ten-membered saturated, partially unsaturated or        aromatic heterocycle which is attached via carbon to the        triazolopyrimidine and contains one to four heteroatoms from the        group consisting of O, N and S,        where R¹ may be partially or fully halogenated or substituted by        one to four identical or different groups R^(a):    -   R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl,        C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkyl,        C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino,        C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyloxy,        C₃-C₆-cycloalkyl, phenyl, naphthyl, a five- to ten-membered        saturated, partially unsaturated or aromatic heterocycle which        contains one to four heteroatoms from the group consisting of O,        N and S, where these aliphatic, alicyclic or aromatic groups for        their part may be partially or fully halogenated or carry one to        three groups R^(b):    -   R^(b) is halogen, cyano, nitro, hydroxyl, mercapto, amino,        carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, haloalkyl,        alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkoxy, haloalkoxy,        alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl,        alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy,        alkylaminocarbonyl, dialkylaminocarbonyl,        alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the        alkyl groups in these radicals contain 1 to 6 carbon atoms and        the abovementioned alkenyl or alkynyl groups in these radicals        contain 2 to 8 carbon atoms and the abovementioned groups may be        partially or fully halogenated;        -   and/or one to three of the following radicals:        -   cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy,            where the cyclic systems contain 3 to 10 ring members; aryl,            aryloxy, arylthio, aryl-C₁-C₆-alkoxy, aryl-C₁-C₆-alkyl,            hetaryl, hetaryloxy, hetarylthio, where the aryl radicals            preferably contain 6 to 10 ring members and the hetaryl            radicals 5 or 6 ring members, where the cyclic systems may            be partially or fully halogenated or substituted by alkyl or            haloalkyl groups;

-   R² is C₁-C₄-alkyl which may be substituted by halogen, cyano, nitro    or C₁-C₂-alkoxy;

-   n is 0 or an integer from 1 to 4;

-   R is halogen, cyano, C₁-C₆-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl,    C₁-C₆-haloalkyl, C₂-C₁₀-haloalkenyl, C₁-C₆-alkoxy,    C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₁-C₆-haloalkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy,    C₁-C₈-alkoxycarbonyl, C₂-C₁₀-alkenyloxycarbonyl,    C₂-C₁₀-alkynyloxycarbonyl, aminocarbonyl, C₁-C₈-alkylaminocarbonyl,    di-(C₁-C₈-)alkylaminocarbonyl, C₁-C₈-alkoximinoalkyl,    C₂-C₁₀-alkenyloximinoalkyl, C₂-C₁₀-alkynyloximinoalkyl,    C₁-C₈-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₂-C₁₀-alkynylcarbonyl,    C₃-C₆-cycloalkylcarbonyl, or a five- to ten-membered saturated,    partially unsaturated or aromatic heterocycle which contains one to    four heteroatoms from the group consisting of O, N and S;

-   X is SO_(m)—R^(x), NR^(x)R^(y) or NR^(x)—(C═O)—R^(y);    -   R^(X), R^(Y) are: hydrogen, C₁-C₆-alkyl, C₂-C₁₀-alkenyl,        C₂-C₁₀-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, where the        above radicals may be partially or fully halogenated or        substituted by cyano, C₁-C₄-alkoximino, C₂-C₄-alkenyloximino,        C₂-C₄-alkynyloximino or C₁-C₄-alkoxy;

-   m is 0 or an integer 1 to 3.

Moreover, the invention relates to a process for preparing thesecompounds, to compositions comprising them and to their use forcontrolling harmful fungi.

5-chlorotriazolopyrimidines for controlling harmful fungi are disclosedin EP-A 71 792, EP-A 550 113, WO-A 94/20501, EP-A 834 513, WO-A 98/46608and WO-A 99/41255.

However, in many cases, their activity is unsatisfactory. It is anobject of the invention to provide compounds having improved activity.

We have found that this object is achieved by the compounds defined atthe outset. Furthermore, we have found processes for their preparation,compositions comprising them and methods for controlling harmful fungiusing the compounds I.

The compounds of the formula I differ from the compounds in theabovementioned publications in that the 5-alkyl radical is combined withgroups in position 7 which are attached via carbon.

Compared to the known compounds, the compounds of the formula I haveincreased activity against harmful fungi.

The compounds I can be obtained by different routes; advantageously,5-aminotriazole of the formula II is used as starting material andcondensed with dicarbonyl compounds of the formula III.

This reaction usually takes place at temperatures of from 80° C. to 250°C., preferably from 120° C. to 180° C., in the absence of a solvent orin an inert organic solvent in the presence of a base [cf. EP-A 770 615]or in the presence of acetic acid under the conditions known from Adv.Het. Chem. 57 (1993), 81 ff.

Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons suchas toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers,nitriles, ketones, alcohols, and also N-methylpyrrolidone, dimethylsulfoxide, dimethylformamide and dimethylacetamide. The reaction isparticularly preferably carried out in the absence of a solvent or inethylene glycol dimethyl ether, chlorobenzene, xylene, dimethylsulfoxide or N-methylpyrrolidone. It is also possible to use mixtures ofthe solvents mentioned.

Suitable bases are, in general, inorganic compounds, such as alkalimetal and alkaline earth metal hydroxides, alkali metal and alkalineearth metal oxides, alkali metal and alkaline earth metal hydrides,alkali metal amides, alkali metal and alkaline earth metal carbonatesand also alkali metal bicarbonates, organometallic compounds, inparticular alkali metal alkyls, alkylmagnesium halides and also alkalimetal and alkaline earth metal alkoxides and dimethoxymagnesium,moreover organic bases, for example tertiary amines, such astrimethylamine, triethylamine, diisopropylethylamine, tributylamine andN-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines,such as collidine, lutidine and 4-dimethylaminopyridine, and alsobicyclic amines. Particular preference is given to tertiary amines suchas triisopropylamine, tributylamine, N-methylmorpholine orN-methylpiperidine.

The bases are generally employed in catalytic amounts; however, they canalso be employed in equimolar amounts, in excess or, if appropriate, assolvent.

The starting materials are generally reacted with one another inequimolar amounts. In terms of yield, it may be advantageous to employan excess of base and diketone III, based on II.

The diketones III can be prepared analogously to processes known fromthe literature, for example as described in the publications mentionedabove. Diketones having an acylamino substituent can be obtained, forexample, by acylation from the corresponding amino group compound. Ingeneral, the amino grouping can be introduced into the phenyl ring byreducing a suitable nitro precursor. The sulfonic acid grouping can beintroduced into the phenyl ring by direct sulfonylation of a suitableprecursor using sulfuric acid or oleum. However, the sulfonic acidgrouping can also be synthesized from a suitable diazonium salt bySandmeyer reaction with sulfur trioxide. The diazonium salt can beobtained from the abovementioned amino compound. The sulfoxides andsulfones can be prepared by oxidizing the corresponding alkyl arylsulfides by processes known from the literature using, for example,hydrogen peroxide, peracids or selenium dioxide.

Compounds of the formula I can also be obtained by coupling5-halotriazolopyrimidines of the formula IV (Y is halogen, in particularchlorine or bromine) with organometallic reagents of the formula VII.

In the formula VII, M is a metal ion having the valency Y, such as, forexample, B, Zn, Mg or Sn. In one embodiment of this process, thereaction is carried out with transition metal catalysis, such as Ni orPd catalysis. This reaction can be carried out, for example, analogouslyto the following methods: J. Chem. Soc. Perkin Trans. 1 (1994), 1187,ibid (1996), 2345; WO-A 99/41255; Aust. J. Chem. 43 (1990), 733; J. Org.Chem. 43 (1978), 358; J. Chem. Soc. Chem. Commun. (1979), 866;Tetrahedron Lett. 34 (1993), 8267; ibid 33 (1992), 413. In particular incases where M is Zn or Mg, the reaction can also be carried out in theabsence of a catalyst. The compounds IV are known from the publicationscited at the outset. They are obtained, in particular, from5,7-dichlorotriazolopyrimidines by introducing the radical R¹ usingorganometallic processes similar to those described above.

The compounds of the formula I′ according to the invention can also beobtained by reacting 5-halotriazolopyrimidines of the formula IV withsubstituted malonic acid esters of the formula V, where Rx isC₁-C₄-alkyl, allyl, phenyl or benzyl, followed by hydrolysis of theresulting ester VI and decarboxylation of the carboxylic acid VIa.

In the formula IV, Y is halogen, in particular chlorine or bromine. Thecompounds IV are known from the publications cited at the outset. In theformula I′, n, R and R¹ have the definitions given for the formula I andR^(A) is hydrogen or C₁-C₃-alkyl which may be substituted by halogen,cyano, nitro or C₁-C₂-alkoxy.

In a preferred embodiment of the process according to the invention,R^(A) is hydrogen or methyl, in particular hydrogen.

The starting materials V are known from the literature [J. Am. Chem.Soc. 64 (1942), 2714; J. Org. Chem. 39 (1974), 2172; Helv. Chim. Acta 61(1978), 1565], or they can be prepared according to the literaturecited.

The subsequent hydrolysis of the ester is carried out under generallyknown conditions [cf.: Greene & Wuts, Protective Groups in OrganicSynthesis, Wiley (1991), p. 224 ff.: Cleavage of alkyl esters under Pdcatalysis (p. 248); hydrolysis of benzyl esters (p. 251); Cleavage ofmethyl or ethyl esters in the presence of lithium salts such as LiI (p.232), LiBr or LiCl; or under acidic or alkaline conditions]. Dependingon the structural elements R^(A), R_(n) and R¹, alkaline or acidichydrolysis of the compounds VI may be advantageous. It is possible thatfull or partial decarboxylation to I′ takes place even under theconditions of ester hydrolysis.

The decarboxylation is usually carried out at temperatures of from 20°C. to 180° C., preferably from 50° C. to 120° C., in an inert solvent,if appropriate in the presence of an acid.

Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid,formic acid, acetic acid, p-toluenesulfonic acid. Suitable solvents arewater, aliphatic hydrocarbons, such as pentane, hexane, cyclohexane andpetroleum ether, aromatic hydrocarbons, such as toluene, o-, m- andp-xylene, halogenated hydrocarbons, such as methylene chloride,chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropylether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran,nitriles, such as acetonitrile and propionitrile, ketones, such asacetone, methyl ethyl ketone, diethyl ketone and tert-butyl methylketone, alcohols, such as methanol, ethanol, n-propanol, isopropanol,n-butanol and tert-butanol, and also dimethyl sulfoxide,dimethylformamide and dimethylacetamide; the reaction is particularlypreferably carried out in hydrochloric acid or acetic acid. It is alsopossible to use mixtures of the solvents mentioned.

The reaction mixtures are worked up in a customary manner, for exampleby mixing with water, phase separation and, if required, chromatographicpurification of the crude products. Some of the intermediates and endproducts are obtained in the form of colorless or slightly brownish,viscous oils, which are purified or freed from volatile components underreduced pressure and at moderately elevated temperatures. If theintermediates and end products are obtained as solids, purification canalso be carried out by recrystallization or digestion.

If individual compounds I cannot be obtained by the routes describedabove, they can be prepared by derivatization of other compounds I.

If the synthesis yields isomer mixtures, a separation is generally notnecessarily required since in some cases the individual isomers can beconverted into one another during the preparation for use or upon use(for example under the action of light, acids or bases). Similarconversions may also occur after use, for example in the treatment ofplants in the treated plant or in the harmful fungus or animal pest tobe controlled.

In the definitions of the symbols given in the above formulae,collective terms were used which generally represent the followingsubstituents:

halogen: fluorine, chlorine, bromine and iodine;

alkyl: saturated, straight-chain or branched hydrocarbon radicals having1 to 4, 6, 8 or 10 carbon atoms, for example C₁-C₆-alkyl such as methyl,ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl,1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl,2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl,1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl,4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl,2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl,1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;

haloalkyl: straight-chain or branched alkyl groups having 1 to 10 carbonatoms (as mentioned above), where all or some of the hydrogen atoms inthese groups may be replaced by halogen atoms as mentioned above, forexample C₁-C₂-haloalkyl such as chloromethyl, bromomethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

alkenyl: unsaturated, straight-chain or branched hydrocarbon radicalshaving 2 to 4, 6, 8 or 10 carbon atoms and a double bond in anyposition, for example C₂-C₆-alkenyl such as ethenyl, 1-propenyl,2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl,1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl,1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl,1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl,4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl,3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl,2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl,4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl,2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl,2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl,1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl,1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;

haloalkenyl: unsaturated, straight-chain or branched hydrocarbonradicals having 2 to 10 carbon atoms and a double bond in any position(as mentioned above), where all or some of the hydrogen atoms in thesegroups may be replaced by halogen atoms as entioned above, in particularby fluorine, chlorine and bromine;

alkynyl: straight-chain or branched hydrocarbon groups having 2 to 4, 6,8 or 10 carbon atoms and a triple bond in any position, for exampleC₂-C₆-alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and1-ethyl-1-methyl-2-propynyl;

cycloalkyl: mono- or bicyclic, saturated hydrocarbon groups having 3 to6, 8, 10 or 12 carbon ring members, for example C₃-C₈-cycloalkyl such ascyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl, or C₇-C₁₂-bicycloalkyl;

aryl: a mono- to trinuclear aromatic ring system comprising 6 to 14carbon ring members, for example phenyl, naphthyl and anthracenyl;

five- to ten-membered saturated, partially unsaturated or aromaticheterocycle which is bonded to triazolopyrimidine via carbon andcontains one to four heteroatoms from the group consisting of O, N andS:

-   -   5- or 6-membered heterocyclyl which contains one to three        nitrogen atoms and/or one oxygen or sulfur atom or one or two        oxygen and/or sulfur atoms, for example 2-tetrahydrofuranyl,        3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,        2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl,        4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl,        4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl,        4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,        4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,        4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl,        4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl,        1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl,        1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl,        1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl,        1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,        2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,        2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,        2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl,        2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,        2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,        2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,        2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,        2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,        2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,        2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,        2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,        2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl,        2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,        3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl,        3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,        4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,        4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl,        2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,        2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,        3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,        3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl,        3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl,        2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl,        3-hexahydropyridazinyl, 4-hexahydropyridazinyl,        2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl,        5-hexahydropyrimidinyl, 2-piperazinyl,        1,3,5-hexahydro-triazin-2-yl and 1,2,4-hexahydrotriazin-3-yl;    -   5-membered heteroaryl which contains one to four nitrogen atoms        or one to three nitrogen atoms and one sulfur or oxygen atom:        5-membered heteroaryl groups which, in addition to carbon atoms,        may contain one to four nitrogen atoms or one to three nitrogen        atoms and one sulfur or oxygen atom as ring members, for example        2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,        3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,        4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl,        5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,        4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,        1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl,        1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,        1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl        and 1,3,4-triazol-2-yl;    -   benzo-fused 5-membered heteroaryl which contains one to three        nitrogen atoms or one nitrogen atom and one oxygen or sulfur        atom: 5-membered heteroaryl groups which, in addition to carbon        atoms, may contain one to four nitrogen atoms or one to three        nitrogen atoms and one sulfur or oxygen atom as ring members and        in which two adjacent carbon ring members or a nitrogen and an        adjacent carbon ring member may be bridged by a        buta-1,3-diene-1,4-diyl group;    -   6-membered heteroaryl which contains one to three or one to four        nitrogen atoms: 6-membered heteroaryl groups which, in addition        to carbon atoms, may contain one to three or one to four        nitrogen atoms as ring members, for example 2-pyridinyl,        3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,        2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,        1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

The scope of the present invention includes the (R) and (S) isomers andthe racemates of compounds of the formula I having chiral centers.

With a view to the intended use of the triazolopyrimidines of theformula I, the following meanings of the substituents are particularlypreferred, in each case on their own or in combination:

Preference is given to compounds I in which R¹ is C₃-C₈-alkyl,C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl.

Particular preference is given to compounds I in which R¹ is C₁-C₈-alkylor C₁-C₆-haloalkyl.

Additionally, preference is given to compounds I in which R¹ isC₂-C₁₀-alkynyl and in particular C₂-C₁₀-alkenyl. Particular preferenceis given to branched C₂-C₁₀-alkenyl.

Preference is likewise given to compounds I in which R¹ is a 5- or6-membered saturated or aromatic heterocycle which is attached viacarbon.

Moreover, particular preference is given to compounds I in which R¹ isC₃-C₆-cycloalkyl or C₅-C₆-cycloalkyl which may be substituted byC₁-C₄-alkyl.

Particular preference is given to compounds I in which R^(a) is halogen,cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoximino, C₂-C₆-alkenyloximino,C₂-C₆-alkynyloximino, C₃-C₆-cycloalkyl or C₅-C₆-cycloalkenyl, where thealiphatic or alicyclic groups for their part may be partially or fullyhalogenated or may carry one to three groups R^(b).

Particular preference is given to compounds I in which R^(b) is halogen,cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylcarbonyl,C₁-C₆-haloalkylcarbonyl or C₁-C₆-alkoxy.

Particular preference is also given to compounds I in which R² isC₁-C₄-alkyl which may be substituted by halogen.

Particular preference is likewise given to compounds I in which R² ismethyl.

In addition, preference is given to compounds I in which R² ishalomethyl.

Particular preference is also given to compounds I in which asubstituent R is located in the 2-position and n is an integer from 1 to3, in particular 1 or 2.

Moreover, particular preference is given to compounds I in which n is 2or 3 and a substituent R is located in the 2-position.

Preference is furthermore given to compounds I in which R is fluorine,chlorine, bromine, cyano, C₁-C₆-alkyl or C₁-C₆-alkoxy.

Particular preference is likewise given to compounds I in which R isfluorine, chlorine, methyl, trifluoromethyl or methoxy.

In addition, particular preference is given to compounds I in whichR_(n) is 2-chloro, 2-fluoro, 2-methyl, 2-methoxy, 2-trifluoromethyl,2-trifluoromethyl-6-chloro, 2-chloro-6-fluoro, 2,6-difluoro,2-fluoro-6-methyl, 2,4-difluoro, 2-fluoro-4-chloro, 2-fluoro-3-methyl,2-fluoro-4-methyl, 2-chloro-4-fluoro, 2,4-dichloro, 2-chloro-4-methyl,2-chloro-3-methyl, 2,6-dichloro, 2-chloro-6-methyl, 2-methyl-4-fluoro,2-methyl-4-chloro, 2,4-dimethyl, 2,3-dimethyl, 2-methyl-6-fluoro,2-methyl-6-chloro or 2,6-dimethyl.

Moreover, particular preference is given to compounds I in which X isC₁-C₆-alkylsulfonyl, C₁-C₆-alkylsulfenyl, C₁-C₆-alkylsulfoxyl,C₁-C₆-alkylmercapto, amino, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino,C₁-C₆-alkylcarbonylamino, C₁-C₆-alkylcarbonyl (C₁-C₆-alkyl) amino.

Preference is given to compounds I in which the substituent X is locatedin the 3- or 5-position on the phenyl ring.

Especially preferred are compounds I in which the substituent X islocated in the 4-position on the phenyl ring.

Particular preference is likewise given to compounds I in which m is 1or 2. The sulfur atom is preferably attached directly to the phenylring. If m is 2 or 3, the sulfur may also be attached to the phenyl ringvia oxygen.

Particular preference is given to triazolopyrimidines of the formula I′

where the index and the substituents are as defined below:

-   R¹ is C₃-C₈-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₆-cycloalkyl,    C₅-C₆-cycloalkenyl; where R¹ may be partially or fully halogenated    or substituted by one to four identical or different groups R^(a):    -   R^(a) is halogen, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl,        C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl,        C₁-C₆-alkoximino, C₂-C₆-alkenyloximino, C₂-C₆-alkynyloximino;-   R² is C₁-C₄-alkyl which may be substituted by halogen;-   n is an integer from 0 to 2;-   R is fluorine, chlorine, bromine, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy;-   X is SO—R^(x), SO₂—R^(x) or NR^(x)—(C═O)—R^(y);    -   R^(x), R^(y) are: hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or        C₃-C₆-cycloalkyl, where the above radicals may be partially or        fully halogenated.

With a view to their use, most particular preference is given to thecompounds IA compiled in the tables below. Moroever, the groupsmentioned in the tables for a substituent are themselves, independentlyof the combination in which they are mentioned, a particularly preferredembodiment of the substituent in question.

Table 1

Compounds of the formula IA in which R_(n) is 2-chloro, X is acetylaminoand R¹ for each compound corresponds to one row of table A

Table 2

Compounds of the formula IA in which R_(n) is 2-fluoro, X is acetylaminoand R¹ for each compound corresponds to one row of table A

Table 3

Compounds of the formula IA in which R_(n) is 2-methyl, X is acetylaminoand R¹ for each compound corresponds to one row of table A

Table 4

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 5

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 6

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 7

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 8

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 9

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 10

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 11

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, x isacetylamino and R¹ for each compound corresponds to one row of table A

Table 12

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isacetylamino and R¹ for each compound corresponds to one row of table A

Table 13

Compounds of the formula IA, in which R_(n) is 2-chloro, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 14

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 15

Compounds of the formula IA, in which R_(n) is 2-methyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 16

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 17

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 18

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 19

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 20

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 21

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 22

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 23

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 24

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isN-acetyl-N-methylamino and R¹ for each compound corresponds to one rowof table A

Table 25

Compounds of the formula IA, in which R_(n) is 2-chloro, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 26

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 27

Compounds of the formula IA, in which R_(n) is 2-methyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 28

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 29

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 30

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 31

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 32

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 33

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 34

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 35

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 36

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isN-acetyl-N-ethylamino and R¹ for each compound corresponds to one row oftable A

Table 37

Compounds of the formula IA, in which R_(n) is 2-chloro, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 38

Compounds of the formula IA, in which R_(n) is 2-fluoro, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 39

Compounds of the formula IA, in which R_(n) is 2-methyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 40

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 41

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 42

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 43

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 44

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 45

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 46

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 47

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 48

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X ispropionylamino and R¹ for each compound corresponds to one row of tableA

Table 49

Compounds of the formula IA, in which R_(n) is 2-chloro, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 50

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 51

Compounds of the formula IA, in which R_(n) is 2-methyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 52

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 53

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 54

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A Table 55

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 56

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 57

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 58

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 59

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 60

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isN-propionyl-N-methylamino and R¹ for each compound corresponds to onerow of table A

Table 61

Compounds of the formula IA, in which R_(n) is 2-chloro, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 62

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 63

Compounds of the formula IA, in which R_(n) is 2-methyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 64

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 65

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 66

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 67

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 68

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 69

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 70

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 71

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 72

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isN-propionyl-N-ethylamino and R¹ for each compound corresponds to one rowof table A

Table 73

Compounds of the formula IA, in which R_(n) is 2-chloro, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 74

Compounds of the formula IA, in which R_(n) is 2-fluoro, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 75

Compounds of the formula IA, in which R_(n) is 2-methyl, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 76

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 77

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 78

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 79

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 80

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 81

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 82

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 83

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, x is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 84

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X is2-methylpropionylamino and R¹ for each compound corresponds to one rowof table A

Table 85

Compounds of the formula IA, in which R_(n) is 2-chloro, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 86

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 87

Compounds of the formula IA, in which R_(n) is 2-methyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 88

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 89

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 90

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 91

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 92

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 93

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 94

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 95

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 96

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isN-2-methylpropionyl-N-methylamino and R¹ for each compound correspondsto one row of table A

Table 97

Compounds of the formula IA, in which R_(n) is 2-chloro, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 98

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 99

Compounds of the formula IA, in which R_(n) is 2-methyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 100

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 101

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 102

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 103

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 104

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 105

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 106

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 107

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 108

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isN-2-methylpropionyl-N-ethylamino and R¹ for each compound corresponds toone row of table A

Table 109

Compounds of the formula IA, in which R_(n) is 2-chloro, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 110

Compounds of the formula IA, in which R_(n) is 2-fluoro, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 111

Compounds of the formula IA, in which R_(n) is 2-methyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 112

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 113

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 114

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 115

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 116

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 117

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 118

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 119

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 120

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X ismethylsulfonyl and R¹ for each compound corresponds to one row of tableA

Table 121

Compounds of the formula IA, in which R_(n) is 2-chloro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 122

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 123

Compounds of the formula IA, in which R_(n) is 2-methyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 124

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 125

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 126

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 127

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 128

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 129

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 130

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 131

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 132

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isethylsulfonyl and R¹ for each compound corresponds to one row of table A

Table 133

Compounds of the formula IA, in which R_(n) is 2-chloro, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 134

Compounds of the formula IA, in which R_(n) is 2-fluoro, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 135

Compounds of the formula IA, in which R_(n) is 2-methyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 136

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 137

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 138

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 139

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 140

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 141

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 142

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 143

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 144

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X is2-methylpropylsulfonyl and R¹ for each compound corresponds to one rowof table A

Table 145

Compounds of the formula IA, in which R_(n) is 2-chloro, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 146

Compounds of the formula IA, in which R_(n) is 2-fluoro, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 147

Compounds of the formula IA, in which R_(n) is 2-methyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 148

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 149

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 150

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 151

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 152

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 153

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 154

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 155

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 156

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X ismethylsulfoxyl and R¹ for each compound corresponds to one row of tableA

Table 157

Compounds of the formula IA, in which R_(n) is 2-chloro, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 158

Compounds of the formula IA, in which R_(n) is 2-fluoro, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 159

Compounds of the formula IA, in which R_(n) is 2-methyl, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 160

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 161

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 162

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 163

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 164

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 165

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 166

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 167

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, x isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 168

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X isethylsulfoxyl and R¹ for each compound corresponds to one row of table A

Table 169

Compounds of the formula IA, in which R_(n) is 2-chloro, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 170

Compounds of the formula IA, in which R_(n) is 2-fluoro, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 171

Compounds of the formula IA, in which R_(n) is 2-methyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 172

Compounds of the formula IA, in which R_(n) is 2,6-dichloro, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 173

Compounds of the formula IA, in which R_(n) is 2,6-difluoro, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 174

Compounds of the formula IA, in which R_(n) is 2,6-dimethyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 175

Compounds of the formula IA, in which R_(n) is 2-chloro-3-methyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 176

Compounds of the formula IA, in which R_(n) is 2-fluoro-3-methyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 177

Compounds of the formula IA, in which R_(n) is 2,3-dimethyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 178

Compounds of the formula IA, in which R_(n) is 2-chloro-6-fluoro, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 179

Compounds of the formula IA, in which R_(n) is 2-chloro-6-methyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A

Table 180

Compounds of the formula IA, in which R_(n) is 2-fluoro-6-methyl, X is2-methylpropylsulfoxyl and R¹ for each compound corresponds to one rowof table A TABLE A No. R¹ A-1 CH₃ A-2 CH₂CH₃ A-3 CH₂CH₂CH₃ A-4 CH(CH₃)₂A-5 CH₂CH(CH₃)₂ A-6 (±)CH(CH₃)CH₂CH₃ A-7 (R)CH(CH₃)CH₂CH₃ A-8(S)CH(CH₃)CH₂CH₃ A-9 (CH₂)₃CH₃ A-10 C(CH₃)₃ A-11 (CH₂)₄CH₃ A-12CH(CH₂CH₃)₂ A-13 CH₂CH₂CH(CH₃)₂ A-14 (±)CH(CH₃)(CH₂)₂CH₃ A-15(R)CH(CH₃)(CH₂)₂CH₃ A-16 (S)CH(CH₃)(CH₂)₂CH₃ A-17 (±)CH₂CH(CH₃)CH₂CH₃A-18 (R CH₂CH(CH₃)CH₂CH₃ A-19 (S)CH₂CH(CH₃)CH₂CH₃ A-20(±)CH(CH₃)CH(CH₃)₂ A-21 (R)CH(CH₃)CH(CH₃)₂ A-22 (S)CH(CH₃)CH(CH₃)₂ A-23(CH₂)₅CH₃ A-24 (±,±)CH(CH₃)CH(CH₃)CH₂CH₃ A-25 (±,R)CH(CH₃)CH(CH₃)CH₂CH₃A-26 (±,S)CH(CH₃)CH(CH₃)CH₂CH₃ A-27 (±)CH₂CH(CH₃)CF₃ A-28(R)CH₂CH(CH₃)CF₃ A-29 (S)CH₂CH(CH₃)CF₃ A-30 (±)CH₂CH(CF₃)CH₂CH₃ A-31(R)CH₂CH(CF₃)CH₂CH₃ A-32 (S)CH₂CH(CF₃)CH₂CH₃ A-33 (±,±)CH(CH₃)CH(CH₃)CF₃A-34 (±,R)CH(CH₃)CH(CH₃)CF₃ A-35 (±,S)CH(CH₃)CH(CH₃)CF₃ A-36(±,±)CH(CH₃)CH(CF₃)CH₂CH₃ A-37 (±,R)CH(CH₃)CH(CF₃)CH₂CH₃ A-38(±,S)CH(CH₃)CH(CF₃)CH₂CH₃ A-39 CF₃ A-40 CF₂CF₃ A-41 CF₂CF₂CF₃ A-42c-C₃H₅ A-43 (1-CH₃)-c-C₃H₄ A-44 c-C₅H₉ A-45 c-C₆H₁₁ A-46 (4-CH₃)-c-C₆H₁₀A-47 CH₂C(CH₃)═CH₂ A-48 CH₂CH₂C(CH₃)═CH₂ A-49 CH₂—C(CH₃)₃ A-50CH₂—Si(CH₃)₃ A-51 n-C₆H₁₃ A-52 (CH₂)₃—CH(CH₃)₂ A-53 (CH₂)₂—CH(CH₃)—C₂H₅A-54 CH₂—CH(CH₃)-n-C₃H₇ A-55 CH(CH₃)-n-C₄H₉ A-56 CH₂—CH(C₂H₅)₂ A-57CH(C₂H₅)-n-C₃H₇ A-58 CH₂-c-C₅H₉ A-59 CH₂—CH(CH₃)—CH(CH₃)₂ A-60CH(CH₃)—CH₂CH(CH₃)₂ A-61 CH(CH₃)—CH(CH₃)—C₂H₅ A-62 CH(CH₃)—C(CH₃)₃ A-63(CH₂)₂—C(CH₃)₃ A-64 CH₂—C(CH₃)₂—C₂H₅ A-65 2-CH₃-c-C₅H₈ A-66 3-CH₃-c-C₅H₈A-67 C(CH₃)₂-n-C₃H₇ A-68 (CH₂)₆—CH₃ A-69 (CH₂)₄—CH(CH₃)₂ A-70(CH₂)₃—CH(CH₃)—C₂H₅ A-71 (CH₂)₂—CH(CH₃)-n-C₃H₇ A-72 CH₂—CH(CH₃)-n-C₄H₉A-73 CH(CH₃)-n-C₅H₁₁ A-74 (CH₂)₃C(CH₃)₃ A-75 (CH₂)₂CH(CH₃)—CH(CH₃)₂ A-76(CH₂)CH(CH₃)—CH₂CH(CH₃)₂ A-77 CH(CH₃)(CH₂)₂—CH(CH₃)₂ A-78(CH₂)₂C(CH₃)₂C₂H₅ A-79 CH₂CH(CH₃)CH(CH₃)C₂H₅ A-80 CH(CH₃)CH₂CH(CH₃)C₂H₅A-81 CH₂C(CH₃)₂-n-C₃H₇ A-82 CH(CH₃)CH(CH₃)-n-C₃H₇ A-83 C(CH₃)₂-n-C₄H₉A-84 (CH₂)₂CH(C₂H₅)₂ A-85 CH₂CH(C₂H₅)-n-C₃H₇ A-86 CH(C₂H₅)-n-C₄H₉ A-87CH₂CH(CH₃)C(CH₃)₃ A-88 CH(CH₃)CH₂C(CH₃)₃ A-89 CH₂C(CH₃)₂CH(CH₃)₂ A-90CH₂CH(C₂H₅)CH(CH₃)₂ A-91 CH(CH₃)CH(CH₃)CH(CH₃)₂ A-92 C(CH₃)₂CH₂CH(CH₃)₂A-93 CH(C₂H₅)CH₂CH(CH₃)₂ A-94 CH(CH₃)C(CH₃)₂C₂H₅ A-95 CH(CH₃)CH(C₂H₅)₂A-96 C(CH₃)₂CH(CH₃)C₂H₅ A-97 CH(C₂H₅)CH(CH₃)C₂H₅ A-98C(CH₃)(C₂H₅)-n-C₃H₇ A-99 CH(n-C₃H₇)₂ A-100 CH(n-C₃H₇)CH(CH₃)₂ A-101C(CH₃)₂C(CH₃)₃ A-102 C(CH₃)(C₂H₅)—CH(CH₃)₂ A-103 C(C₂H₅)₃ A-104(3-CH₃)-c-C₆H₁₀ A-105 (2-CH₃)-c-C₆H₁₀ A-106 n-C₈H₁₇ A-107CH₂C(═NO—CH₃)CH₃ A-108 CH₂C(═NO—C₂H₅)CH₃ A-109 CH₂C(═NO-n-C₃H₇)CH₃ A-110CH₂C(═NO-i-C₃H₇)CH₃ A-111 CH(CH₃)C(═NOCH₃)CH₃ A-112 CH(CH₃)C(═NOC₂H₅)CH₃A-113 CH(CH₃)C(═NO-n-C₃H₇)CH₃ A-114 CH(CH₃)C(═NO-i-C₃H₇)CH₃ A-115C(═NOCH₃)C(═NOCH₃)CH₃ A-116 C(═NOCH₃)C(═NOC₂H₅)CH₃ A-117C(═NOCH₃)C(═NO-n-C₃H₇)CH₃ A-118 C(═NOCH₃)C(═NO-i-C₃H₇)CH₃ A-119C(═NOC₂H₅)C(═NOCH₃)CH₃ A-120 C(═NOC₂H₅)C(═NOC₂H₅)CH₃ A-121C(═NOC₂H₅)C(═NO-n-C₃H₇)CH₃ A-122 C(═NOC₂H₅)C(═NO-i-C₃H₇)CH₃ A-123CH₂C(═NO—CH₃)C₂H₅ A-124 CH₂C(═NO—C₂H₅)C₂H₅ A-125 CH₂C(═NO-n-C₃H₇)C₂H₅A-126 CH₂C(═NO-i-C₃H₇)C₂H₅ A-127 CH(CH₃)C(═NOCH₃)C₂H₅ A-128CH(CH₃)C(═NOC₂H₅)C₂H₅ A-129 CH(CH₃)C(═NO-n-C₃H₇)C₂H₅ A-130CH(CH₃)C(═NO-n-C₃H₇)C₂H₅ A-131 C(═NOCH₃)C(═NOCH₃)C₂H₅ A-132C(═NOCH₃)C(═NOC₂H₅)C₂H₅ A-133 C(═NOCH₃)C(═NO-n-C₃H₇)C₂H₅ A-134C(═NOCH₃)C(═NO-i-C₃H₇)C₂H₅ A-135 C(═NOC₂H₅)C(═NOCH₃)C₂H₅ A-136C(═NOC₂H₅)C(═NOC₂H₅)C₂H₅ A-137 C(═NOC₂H₅)C(═NO-n-C₃H₇)C₂H₅ A-138C(═NOC₂H₅)C(═NO-i-C₃H₇)C₂H₅ A-139 CH═CH—CH₂CH₃ A-140 CH₂—CH═CH—CH₃ A-141CH₂—CH₂—CH═CH₂ A-142 C(CH₃)₂CH₂CH₃ A-143 CH═C(CH₃)₂ A-144 C(═CH₂)—CH₂CH₃A-145 C(CH₃)═CH—CH₃ A-146 CH(CH₃)CH═CH₂ A-147 CH═CH-n-C₃H₇ A-148CH₂—CH═CH—C₂H₅ A-149 (CH₂)₂—CH═CH—CH₃ A-150 (CH₂)₃—CH═CH₂ A-151CH═CH—CH(CH₃)₂ A-152 CH₂—CH═C(CH₃)₂ A-153 (CH₂)₂—C(CH₃)═CH₂ A-154CH═C(CH₃)—C₂H₅ A-155 CH₂—C(═CH₂)—C₂H₅ A-156 CH₂—C(CH₃)═CH—CH₃ A-157CH₂—CH(CH₃)—CH═CH₂ A-158 C(═CH₂)—CH₂—CH₂—CH₃ A-159 C(CH₃)═CH—CH₂—CH₃A-160 CH(CH₃)—CH═CH—CH₃ A-161 CH(CH₃)—CH₂—CH═CH₂ A-162 C(═CH₂)CH(CH₃)₂A-163 C(CH₃)═C(CH₃)₂ A-164 CH(CH₃)—C(═CH₂)—CH₃ A-165 C(CH₃)₂—CH═CH₂A-166 C(C₂H₅)═CH—CH₃ A-167 CH(C₂H₅)—CH═CH₂ A-168 CH═CH—CH₂—CH₂—CH₂—CH₃A-169 CH₂—CH═CH—CH₂—CH₂—CH₃ A-170 CH₂—CH₂—CH═CH—CH₂—CH₃ A-171CH₂—CH₂—CH₂—CH═CH—CH₃ A-172 CH₂—CH₂—CH₂—CH₂—CH═CH₂ A-173CH═CH—CH₂—CH(CH₃)CH₃ A-174 CH₂—CH═CH—CH(CH₃)CH₃ A-175CH₂—CH₂—CH═C(CH₃)CH₃ A-176 CH₂—CH₂—CH₂—C(CH₃)═CH₂ A-177CH═CH—CH(CH₃)—CH₂—CH₃ A-178 CH₂—CH═C(CH₃)—CH₂—CH₃ A-179CH₂—CH₂—C(═CH₂)—CH₂—CH₃ A-180 CH₂—CH₂—C(CH₃)═CH—CH₃ A-181CH₂—CH₂—CH(CH₃)—CH═CH₂ A-182 CH═C(CH₃)—CH₂—CH₂—CH₃ A-183CH₂—C(═CH₂)—CH₂—CH₂—CH₃ A-184 CH₂—C(CH₃)═CH—CH₂—CH₃ A-185CH₂—CH(CH₃)—CH═CH—CH₃ A-186 CH₂—CH(CH₃)—CH₂—CH═CH₂ A-187C(═CH₂)—CH₂—CH₂—CH₂—CH₃ A-188 C(CH₃)═CH—CH₂—CH₂—CH₃ A-189CH(CH₃)—CH═CH—CH₂—CH₃ A-190 CH(CH₃)—CH₂—CH═CH—CH₃ A-191CH(CH₃)—CH₂—CH₂—CH═CH₂ A-192 CH═CH—C(CH₃)₃ A-193 CH═C(CH₃)—CH(CH₃)—CH₃A-194 CH₂—C(═CH₂)—CH(CH₃)—CH₃ A-195 CH₂—C(CH₃)═C(CH₃)—CH₃ A-196CH₂—CH(CH₃)—C(═CH₂)—CH₃ A-197 C(═CH₂)—CH₂—CH(CH₃)—CH₃ A-198C(CH₃)═CH—CH(CH₃)—CH₃ A-199 CH(CH₃)—CH═C(CH₃)—CH₃ A-200CH(CH₃)—CH₂—C(═CH₂)—CH₃ A-201 CH═C(CH₂—CH₃)—CH₂—CH₃ A-202CH₂—C(═CH—CH₃)—CH₂—CH₃ A-203 CH₂—CH(CH═CH₂)—CH₂—CH₃ A-204C(═CH—CH₃)—CH₂—CH₂—CH₃ A-205 CH(CH═CH₂)—CH₂—CH₂—CH₃ A-206C(CH₂—CH₃)═CH—CH₂—CH₃ A-207 CH(CH₂—CH₃)—CH═CH—CH₃ A-208CH(CH₂—CH₃)—CH₂—CH═CH₂ A-209 CH₂—C(CH₃)₂—CH═CH₂ A-210C(═CH₂)—CH(CH₃)—CH₂—CH₃ A-211 C(CH₃)═C(CH₃)—CH₂—CH₃ A-212CH(CH₃)—C(═CH₂)—CH₂—CH₃ A-213 CH(CH₃)—C(CH₃)═CH—CH₃ A-214CH(CH₃)—CH(CH₃)—CH═CH₂ A-215 C(CH₃)₂—CH═CH—CH₃ A-216 C(CH₃)₂—CH₂—CH═CH₂A-217 C(═CH₂)—C(CH₃)₃ A-218 C(═CH—CH₃)—CH(CH₃)—CH₃ A-219CH(CH═CH₂)—CH(CH₃)—CH₃ A-220 C(CH₂—CH₃)═C(CH₃)—CH₃ A-221CH(CH₂—CH₃)—C(═CH₂)—CH₃ A-222 C(CH₃)₂—C(═CH₂)—CH₃ A-223C(CH₃)(CH═CH₂)—CH₂—CH₃ A-224 C(CH₃)(CH₂CH₃)—CH₂—CH₂—CH₃ A-225CH(CH₂CH₃)—CH(CH₃)—CH₂—CH₃ A-226 CH(CH₂CH₃)—CH₂—CH(CH₃)—CH₃ A-227C(CH₃)₂—C(CH₃)₃ A-228 C(CH₂—CH₃)—C(CH₃)₃ A-229 C(CH₃)(CH₂—CH₃)—CH(CH₃)₂A-230 CH(CH(CH₃)₂)—CH(CH₃)₂ A-231 CH═CH—CH₂—CH₂—CH₂—CH₂—CH₃ A-232CH₂—CH═CH—CH₂—CH₂—CH₂—CH₃ A-233 CH₂—CH₂—CH═CH—CH₂—CH₂—CH₃ A-234CH₂—CH₂—CH₂—CH═CH—CH₂—CH₃ A-235 CH₂—CH₂—CH₂—CH₂—CH═CH—CH₃ A-236CH₂—CH₂—CH₂—CH₂—CH₂—CH═CH₂ A-237 CH═CH—CH₂—CH₂—CH(CH₃)—CH₃ A-238CH₂—CH═CH—CH₂—CH(CH₃)—CH₃ A-239 CH₂—CH₂—CH═CH—CH(CH₃)—CH₃ A-240CH₂—CH₂—CH₂—CH═C(CH₃)—CH₃ A-241 CH₂—CH₂—CH₂—CH₂—C(═CH₂)—CH₃ A-242CH═CH—CH₂—CH(CH₃)—CH₂—CH₃ A-243 CH₂—CH═CH—CH(CH₃)—CH₂—CH₃ A-244CH₂—CH₂—CH═C(CH₃)—CH₂—CH₃ A-245 CH₂—CH₂—CH₂—C(═CH₂)—CH₂—CH₃ A-246CH₂—CH₂—CH₂—C(CH₃)═CH—CH₃ A-247 CH₂—CH₂—CH₂—CH(CH₃)—CH═CH₂ A-248CH═CH—CH(CH₃)—CH₂—CH₂—CH₃ A-249 CH₂—CH═C(CH₃)—CH₂—CH₂—CH₃ A-250CH₂—CH₂—C(═CH₂)—CH₂—CH₂—CH₃ A-251 CH₂—CH₂—C(CH₃)═CH—CH₂—CH₃ A-252CH₂—CH₂—CH(CH₃)—CH═CH—CH₃ A-253 CH₂—CH₂—CH(CH₃)—CH₂—CH═CH₂ A-254CH═C(CH₃)—CH₂—CH₂—CH₂—CH₃ A-255 CH₂—C(═CH₂)—CH₂—CH₂—CH₂—CH₃ A-256CH₂—C(CH₃)═CH—CH₂—CH₂—CH₃ A-257 CH₂—CH(CH₃)—CH═CH—CH₂—CH₃ A-258CH₂—CH(CH₃)—CH₂—CH═CH—CH₃ A-259 CH₂—CH(CH₃)—CH₂—CH₂—CH═CH₂ A-260C(═CH₂)—CH₂—CH₂—CH₂—CH₂—CH₃ A-261 C(CH₃)═CH—CH₂—CH₂—CH₂—CH₃ A-262CH(CH₃)—CH═CH—CH₂—CH₂—CH₃ A-263 CH(CH₃)—CH₂—CH═CH—CH₂—CH₃ A-264CH(CH₃)—CH₂—CH₂—CH═CH—CH₃ A-265 CH(CH₃)—CH₂—CH₂—CH₂—CH═CH₂ A-266CH═CH—CH₂—C(CH₃)₃ A-267 CH₂—CH═CH—C(CH₃)₃ A-268 CH═CH—CH(CH₃)—CH(CH₃)₂A-269 CH₂—CH═C(CH₃)—CH(CH₃)₂ A-270 CH₂—CH₂—C(═CH₂)—CH(CH₃)₂ A-271CH₂—CH₂—C(CH₃)═C(CH₃)₂ A-272 CH₂—CH₂—CH(CH₃)—C(═CH₂)—CH₃ A-273CH═C(CH₃)—CH₂—CH(CH₃)₂ A-274 CH₂—C(═CH₂)—CH₂—CH(CH₃)₂ A-275CH₂—C(CH₃)═CH—CH(CH₃)₂ A-276 CH₂—CH(CH₃)—CH═C(CH₃)₂ A-277CH₂—CH(CH₃)—CH₂—C(═CH₂)—CH₃ A-278 C(═CH₂)—CH₂—CH₂—CH(CH₃)₂ A-279C(CH₃)═CH—CH₂—CH(CH₃)₂ A-280 CH(CH₃)—CH═CH—CH(CH₃)₂ A-281CH(CH₃)—CH₂—CH═C(CH₃)₂ A-282 CH(CH₃)—CH₂—CH₂—C(═CH₂)—CH₃ A-283CH═CH—C(CH₃)₂—CH₂—CH₃ A-284 CH₂—CH₂—C(CH₃)₂—CH═CH₂ A-285CH═C(CH₃)—CH(CH₃)—CH₂—CH₃ A-286 CH₂—C(═CH₂)—CH(CH₃)—CH₂—CH₃ A-287CH₂—C(CH₃)═C(CH₃)—CH₂—CH₃ A-288 CH₂—CH(CH₃)—C(═CH₂)—CH₂—CH₃ A-289CH₂—CH(CH₃)—C(CH₃)═CH—CH₃ A-290 CH₂—CH(CH₃)—CH(CH₃)—CH═CH₂ A-291C(═CH₂)—CH₂—CH(CH₃)—CH₂—CH₃ A-292 C(CH₃)═CH—CH(CH₃)—CH₂—CH₃ A-293CH(CH₃)—CH═C(CH₃)—CH₂—CH₃ A-294 CH(CH₃)—CH₂—C(═CH₂)—CH₂—CH₃ A-295CH(CH₃)—CH₂—C(CH₃)═CH—CH₃ A-296 CH(CH₃)—CH₂—CH(CH₃)—CH═CH₂ A-297CH₂—C(CH₃)₂—CH═CH—CH₃ A-298 CH₂—C(CH₃)₂—CH₂—CH═CH₂ A-299C(═CH₂)—CH(CH₃)—CH₂—CH₂—CH₃ A-300 C(CH₃)═C(CH₃)—CH₂—CH₂—CH₃ A-301CH(CH₃)—C(═CH₂)—CH₂—CH₂—CH₃ A-302 CH(CH₃)—C(CH₃)═CH—CH₂—CH₃ A-303CH(CH₃)—CH(CH₃)—CH═CH—CH₃ A-304 CH(CH₃)—CH(CH₃)—CH₂—CH═CH₂ A-305C(CH₃)₂—CH═CH—CH₂—CH₃ A-306 C(CH₃)₂—CH₂—CH═CH—CH₃ A-307C(CH₃)₂—CH₂—CH₂—CH═CH₂ A-308 CH═CH—CH(CH₂—CH₃)—CH₂—CH₃ A-309CH₂—CH═C(CH₂—CH₃)—CH₂—CH₃ A-310 CH₂—CH₂—C(═CH—CH₃)—CH₂—CH₃ A-311CH₂—CH₂—CH(CH═CH₂)—CH₂—CH₃ A-312 CH═C(CH₂—CH₃)—CH₂—CH₂—CH₃ A-313CH₂—C(═CH—CH₃)—CH₂—CH₂—CH₃ A-314 CH₂—CH(CH═CH₂)—CH₂—CH₂—CH₃ A-315CH₂—C(CH₂—CH₃)═CH—CH₂—CH₃ A-316 CH₂—CH(CH₂—CH₃)—CH═CH—CH₃ A-317CH₂—CH(CH₂—CH₃)—CH—CH═CH₂ A-318 C(═CH—CH₃)—CH₂—CH₂—CH₂—CH₃ A-319CH(CH═CH₂)—CH₂—CH₂—CH₂—CH₃ A-320 C(CH₂—CH₃)═CH—CH₂—CH₂—CH₃ A-321CH(CH₂—CH₃)—CH═CH—CH₂—CH₃ A-322 CH(CH₂—CH₃)—CH₂—CH═CH—CH₃ A-323CH(CH₂—CH₃)—CH₂—CH₂—CH═CH₂ A-324 C(═CH—CH₂—CH₃)—CH₂—CH₂—CH₃ A-325C(CH═CH—CH₃)—CH₂—CH₂—CH₃ A-326 C(CH₂—CH═CH₂)—CH₂—CH₂—CH₃ A-327CH═C(CH₃)—C(CH₃)₃ A-328 CH₂—C(═CH₂)—C(CH₃)₃ A-329CH₂—C(CH₃)₂—CH(═CH₂)—CH₃ A-330 C(═CH₂)—CH(CH₃)—CH(CH₃)—CH₃ A-331C(CH₃)═C(CH₃)—CH(CH₃)—CH₃ A-332 CH(CH₃)—C(═CH₂)—CH(CH₃)—CH₃ A-333CH(CH₃)—C(CH₃)═C(CH₃)—CH₃ A-334 CH(CH₃)—CH(CH₃)—C(═CH₂)—CH₃ A-335C(CH₃)₂—CH═C(CH₃)—CH₃ A-336 C(CH₃)₂—CH₂—C(═CH₂)—CH₃ A-337C(CH₃)₂—C(═CH₂)—CH₂—CH₃ A-338 C(CH₃)₂—C(CH₃)═CH—CH₃ A-339C(CH₃)₂—CH(CH₃)CH═CH₂ A-340 CH(CH₂—CH₃)—CH₂—CH(CH₃)—CH₃ A-341CH(CH₂—CH₃)—CH(CH₃)—CH₂—CH₃ A-342 C(CH₃)(CH₂—CH₃)—CH₂—CH₂—CH₃ A-343CH(i-C₃H₇)—CH₂—CH₂—CH₃ A-344 CH═C(CH₂—CH₃)—CH(CH₃)—CH₃ A-345CH₂—C(═CH—CH₃)—CH(CH₃)—CH₃ A-346 CH₂—CH(CH═CH₂)—CH(CH₃)—CH₃ A-347CH₂—C(CH₂—CH₃)═C(CH₃)—CH₃ A-348 CH₂—CH(CH₂—CH₃)—C(═CH₂)—CH₃ A-349CH₂—C(CH₃)(CH═CH₂)—CH₂—CH₃ A-350 C(═CH₂)—CH(CH₂—CH₃)—CH₂—CH₃ A-351C(CH₃)═C(CH₂—CH₃)—CH₂—CH₃ A-352 CH(CH₃)—C(═CH—CH₃)—CH₂—CH₃ A-353CH(CH₃)—CH(CH═CH₂)—CH₂—CH₃ A-354 CH═C(CH₂—CH₃)—CH(CH₃)—CH₃ A-355CH₂—C(═CH—CH₃)—CH(CH₃)—CH₃ A-356 CH₂—CH(CH═CH₂)—CH(CH₃)—CH₃ A-357CH₂—C(CH₂—CH₃)═C(CH₃)—CH₃ A-358 CH₂—CH(CH₂—CH₃)—C(═CH₂)—CH₃ A-359C(═CH—CH₃)—CH₂—CH(CH₃)—CH₃ A-360 CH(CH═CH₂)—CH₂—CH(CH₃)—CH₃ A-361C(CH₂—CH₃)═CH—CH(CH₃)—CH₃ A-362 CH(CH₂—CH₃)CH═C(CH₃)—CH₃ A-363CH(CH₂—CH₃)CH₂—C(═CH₂)—CH₃ A-364 C(═CH—CH₃)CH(CH₃)—CH₂—CH₃ A-365CH(CH═CH₂)CH(CH₃)—CH₂—CH₃ A-366 C(CH₂—CH₃)═C(CH₃)—CH₂—CH₃ A-367CH(CH₂—CH₃)—C(═CH₂)—CH₂—CH₃ A-368 CH(CH₂—CH₃)—C(CH₃)═CH—CH₃ A-369CH(CH₂—CH₃)—CH(CH₃)—CH═CH₂ A-370 C(CH₃)(CH═CH₂)—CH₂—CH₂—CH₃ A-371C(CH₃)(CH₂—CH₃)—CH═CH—CH₃ A-372 C(CH₃)(CH₂—CH₃)—CH₂—CH═CH₂ A-373C[═C(CH₃)—CH₃]—CH₂—CH₂—CH₃ A-374 CH[C(═CH₂)—CH₃]—CH₂—CH₂—CH₃ A-375C(i-C₃H₇)═CH—CH₂—CH₃ A-376 CH(i-C₃H₇)—CH═CH—CH₃ A-377CH(i-C₃H₇)—CH₂—CH═CH₂ A-378 C(═CH—CH₃)—C(CH₃)₃ A-379 CH(CH═CH₂)—C(CH₃)₃A-380 C(CH₃)(CH═CH₂)CH(CH₃)—CH₃ A-381 C(CH₃)(CH₂—CH₃)C(═CH₂)—CH₃ A-3822-CH₃-cyclohex-1-enyl A-383 [2-(═CH₂)]-c-C₆H₉ A-3842-CH₃-cyclohex-2-enyl A-385 2-CH₃-cyclohex-3-enyl A-3862-CH₃-cyclohex-4-enyl A-387 2-CH₃-cyclohex-5-enyl A-3882-CH₃-cyclohex-6-enyl A-389 3-CH₃-cyclohex-1-enyl A-3903-CH₃-cyclohex-2-enyl A-391 [3-(═CH₂)]-c-C₆H₉ A-3923-CH₃-cyclohex-3-enyl A-393 3-CH₃-cyclohex-4-enyl A-3943-CH₃-cyclohex-5-enyl A-395 3-CH₃-cyclohex-6-enyl A-3964-CH₃-cyclohex-1-enyl A-397 4-CH₃-cyclohex-2-enyl A-3984-CH₃-cyclohex-3-enyl A-399 [4-(═CH₂)]-c-C₆H₉

The compounds I are suitable as fungicides. They have excellent activityagainst a broad spectrum of phytopathogenic fungi, in particular fromthe class of the Ascomycetes, Deuteromycetes, Oomycetes andBasidiomycetes. Some of them act systemically and can be employed incrop protection as foliar- and soil-acting fungicides.

They are especially important for controlling a large number of fungi ina variety of crop plants such as wheat, rye, barley, oats, rice, maize,grass, bananas, cotton, soybean, coffee, sugar cane, grapevines, fruitspecies, ornamentals and vegetable species such as cucumbers, beans,tomatoes, potatoes and cucurbits, and also in the seeds of these plants.

Specifically, they are suitable for controlling the following plantdiseases:

-   -   Alternaria species in vegetables and fruit,    -   Bipolaris and Drechslera species in cereals, rice and lawns,    -   Blumeria graminis (powdery mildew) in cereals,    -   Botrytis cinerea (gray mold) in strawberries, vegetables,        ornamentals and grapevines,    -   Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,    -   Fusarium and Verticillium species in a variety of plants,    -   Mycosphaerella species in cereals, bananas and groundnuts,    -   Phytophthora infestans in potatoes and tomatoes,    -   Plasmopara viticola in grapevines,    -   Podosphaera leucotricha in apples,    -   Pseudocercosporella herpotrichoides in wheat and barley,        Pseudoperonospora species in hops and cucumbers,    -   Puccinia species in cereals,    -   Pyricularia oryzae in rice,    -   Rhizoctonia species in cotton, rice and lawns,    -   Septoria tritici and Stagonospora nodorum in wheat,    -   Uncinula necator in grapevines,    -   Ustilago species in cereals and sugar cane, and    -   Venturia species (scab) in apples and pears.

The compounds I are also suitable for controlling harmful fungi such asPaecilomyces variotii in the protection of materials (for example wood,paper, paint dispersions, fibers or tissues) and in the protection ofstored products.

The compounds I are employed by treating the fungi or the plants, seeds,materials or the soil to be protected against fungal attack with afungicidally effective amount of the active compounds. The applicationcan be carried out before or after the infection of the materials,plants or seeds by the fungi.

The fungicidal compositions generally comprise from 0.1 to 95,preferably from 0.5 to 90% by weight of active compound.

For use in crop protection, the application rates are, depending on thekind of effect desired, from 0.01 to 2.0 kg of active compound per ha.

The treatment of seeds generally requires active compound rates of from0.001 to 0.1 g, preferably from 0.01 to 0.05 g, per kilogram of seed.

For use in the protection of materials or stored products, the activecompound application rate depends on the kind of application area andeffect desired. Customary application rates in the protection ofmaterials are, for example, from 0.001 g to 2 kg, preferably from 0.005g to 1 kg, of active compound per cubic meter of treated material.

The compounds I can be converted into the customary formulations, e.g.solutions, emulsions, suspensions, dusts, powders, pastes and granules.The use form depends on the specific intended use; in any case, itshould ensure fine and uniform distribution of the compound according tothe invention.

The formulations are prepared in a known manner, e.g. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants. Solvents/auxiliaries which are suitable areessentially:

-   -   water, aromatic solvents (for example Solvesso products,        xylene), paraffins (for example mineral oil fractions), alcohols        (for example methanol, butanol, pentanol, benzyl alcohol),        ketones (for example cyclohexanone, gamma-butyrolactone),        pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols,        fatty acid dimethylamides, fatty acids and fatty acid esters. In        principle solvent mixtures may also be used,    -   carriers such as ground natural minerals (e.g. kaolins, clays,        talc, chalk) and ground synthetic minerals (e.g. finely divided        silica, silicates); emulsifiers such as nonionic and anionic        emulsifiers (e.g. polyoxyethylene fatty alcohol ethers,        alkylsulfonates and arylsulfonates), and dispersants such as        lignosulfite waste liquors and methylcellulose.

Suitable surfactants which can be used are the alkali metal, alkalineearth metal and ammonium salts of lignosulfonic acid,naphthalenesulfonic acid, phenolsulfonic acid, anddibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates,alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fattyalcohol glycol ethers, furthermore condensation products of sulfonatednaphthalene and naphthalene derivatives with formaldehyde, condensationproducts of naphthalene or of naphthalene sulfonic acid with phenol andformaldehyde, polyoxyethylene octylphenol ethers, ethoxylatedisooctylphenol, octylphenol and nonylphenol, alkylphenol polyglycolethers, tributylphenyl polyglycol ethers, tristerylphenyl polyglycolethers, alkylaryl polyether alcohols, alcohol and fatty alcohol ethyleneoxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers,ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal,sorbitol esters, lignosulfite waste liquors and methylcellulose aresuitable.

Suitable for preparing directly sprayable solutions, emulsions, pastesor oil dispersions are mineral oil fractions having medium to highboiling points, such as kerosene or diesel fuel, furthermore coal-taroils and oils of plant or animal origin, aliphatic, cyclic and aromatichydrocarbons, for example, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof,methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone,isophorone, strongly polar solvents, for example dimethyl sulfoxide,N-methylpyrrolidone, or water.

Powders, compositions for broadcasting and dusts can be prepared bymixing or joint grinding of the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules andhomogenous granules, can be prepared by binding the active compounds tosolid carriers. Solid carriers are, for example, mineral earths, such assilica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk,bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate,magnesium sulfate, magnesium oxide, ground synthetic materials,fertilizers, such as ammonium sulfate, ammonium phosphate, ammoniumnitrate, ureas and products of plant origin, such as cereal meal, treebark meal, wood meal and nutshell meal, cellulose powders and othersolid carriers.

The formulations generally comprise from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound. The activecompounds are employed in a purity of from 90% to 100%, preferably from95% to 100% (according to the NMR spectrum).

Examples of formulations are: 1. Products for dilution with water

-   A) Water-soluble concentrates (SL)    -   10 parts by weight of a compound according to the invention are        dissolved in water or in a water-soluble solvent. As an        alternative, wetters or other auxiliaries are added. The active        compound dissolves upon dilution with water.-   B) Dispersible concentrates (DC)    -   20 parts by weight of a compound according to the invention are        dissolved in cyclohexanone with addition of a dispersant, for        example polyvinylpyrrolidone. Dilution with water gives a        dispersion.-   C) Emulsifiable concentrates (EC)    -   15 parts by weight of a compound according to the invention are        dissolved in xylene with addition of calcium        dodecylbenzenesulfonate and castor oil ethoxylate (in each case        5%). Dilution with water gives an emulsion.-   D) Emulsions (EW, EO)    -   40 parts by weight of a compound according to the invention are        dissolved in xylene with addition of calcium        dodecylbenzenesulfonate and castor oil ethoxylate (in each case        5%). This mixture is introduced into water by means of an        emulsifying machine (Ultraturrax) and made into a homogeneous        emulsion. Dilution with water gives an emulsion.-   E) Suspensions (SC, OD)    -   In an agitated ball mill, 20 parts by weight of a compound        according to the invention are comminuted with addition of        dispersants, wetters and water or an organic solvent to give a        fine active compound suspension. Dilution with water gives a        stable suspension of the active compound.-   F) Water-dispersible granules and water-soluble granules (WG, SG)    -   50 parts by weight of a compound according to the invention are        ground finely with addition of dispersants and wetters and made        into water-dispersible or water-soluble granules by means of        technical appliances (for example extrusion, spray tower,        fluidized bed). Dilution with water gives a stable dispersion or        solution of the active compound.-   G) Water-dispersible powders and water-soluble powders (WP, SP)    -   75 parts by weight of a compound according to the invention are        ground in a rotor-stator mill with addition of dispersants,        wetters and silica gel. Dilution with water gives a stable        dispersion or solution of the active compound.        2. Products to be applied undiluted-   H) Dustable powders (DP)    -   5 parts by weight of a compound according to the invention are        ground finely and mixed intimately with 95% of finely divided        kaolin. This gives a dustable product.-   I) Granules (GR, FG, GG, MG)    -   0.5 part by weight of a compound according to the invention is        ground finely and associated with 95.5% carriers. Current        methods are extrusion, spray-drying or the fluidized bed. This        gives granules to be applied undiluted.-   J) ULV solutions (UL)    -   10 parts by weight of a compound according to the invention are        dissolved in an organic solvent, for example xylene. This gives        a product to be applied undiluted.

The active compounds can be applied as such, in the form of theirformulations or in the application forms prepared therefrom, for examplein the form of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, compositions forbroadcasting, or granules, by spraying, atomizing, dusting, broadcastingor watering. The application forms depend entirely on the intended uses;in any case, they should ensure very fine dispersion of the activecompounds according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes orwettable powders (spray powders, oil dispersions) by addition of water.To prepare emulsions, pastes or oil dispersions, the substances can behomogenized in water as such or dissolved in an oil or solvent, by meansof wetting agents, tackifiers, dispersants or emulsifiers. However,concentrates comprising active compound, wetting agent, tackifier,dispersant or emulsifier and possibly solvent or oil which are suitablefor dilution with water can also be prepared.

The active compound concentrations in the ready-to-use preparations canbe varied over a relatively wide range. In general, they are from 0.0001to 10%, preferably from 0.01 to 1%.

It is also possible to use the active compounds with a high degree ofsuccess in the ultra-low-volume method (ULV), it being possible to applyformulations comprising more than 95% by weight of active compound oreven the active compound without additives.

Oils of various types, wetting agents, adjuvants, herbicides,fungicides, other pesticides and bactericides can be added to the activecompounds, if desired even immediately prior to application (tank mix).These agents can be added to the compositions according to the inventionin a weight ratio of 1:10 to 10:1.

The compositions according to the invention in the use form asfungicides may also be present in combination with other activecompounds, for example with herbicides, insecticides, growth regulators,fungicides or else with fertilizers. In many cases, mixing of thecompounds I, or of the compositions comprising them, in the use form asfungicides with other fungicides results in a broader fungicidalspectrum of activity.

The following list of fungicides, in combination with which thecompounds according to the invention can be used, is intended toillustrate the possible combinations, but not to impose any limitation:

-   -   acylalanines, such as benalaxyl, metalaxyl, ofurace or oxadixyl,    -   amine derivatives, such as aldimorph, dodine, dodemorph,        fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine        or tridemorph,    -   anilinopyrimidines, such as pyrimethanil, mepanipyrim or        cyprodinyl,    -   antibiotics, such as cycloheximide, griseofulvin, kasugamycin,        natamycin, polyoxin or streptomycin,    -   azoles, such as bitertanol, bromoconazole, cyproconazole,        difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole,        fluquinconazole, flusilazole, hexaconazole, imazalil,        metconazole, myclobutanil, penconazole, propiconazole,        prochloraz, prothioconazole, tebuconazole, triadimefon,        triadimenol, triflumizole or triticonazole,    -   dicarboximides, such as iprodione, myclozolin, procymidone or        vinclozolin,    -   dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam,        metiram, propineb, polycarbamate, thiram, ziram or zineb,    -   heterocyclic compounds, such as anilazine, benomyl, boscalid,        carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet,        dithianon, famoxadone, fenamidone, fenarimol, fuberidazole,        flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol,        probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen,        silthiofam, thiabendazole, thifluzamide, thiophanate-methyl,        tiadinil, tricyclazole or triforine,    -   copper fungicides, such as Bordeaux mixture, copper acetate,        copper oxychloride or basic copper sulfate,    -   nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton        or nitrophthal-isopropyl    -   phenylpyrroles, such as fenpiclonil or fludioxonil,    -   sulfur    -   other fungicides, such as acibenzolar-S-methyl, benthiavalicarb,        carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet,        diclomezine, diclocymet, diethofencarb, edifenphos, ethaboxam,        fenhexamid, fentin acetate, fenoxanil, ferimzone, fluazinam,        fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene,        metrafenone, pencycuron, propamocarb, phthalide,        tolclofos-methyl, quintozene or zoxamide    -   strobilurins, such as azoxystrobin, dimoxystrobin,        fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin,        picoxystrobin, pyraclostrobin or trifloxystrobin,    -   sulfenic acid derivatives, such as captafol, captan,        dichlofluanid, folpet or tolylfluanid    -   cinnamides and analogous compounds, such as dimethomorph,        flumetover or flumorph.

SYNTHESIS EXAMPLES

The procedures described in the synthesis examples below were used toprepare further compounds I by appropriate modification of the startingcompounds. The compounds thus obtained are listed in the tables below,together with physical data.

Example 1 Preparation of5-methyl-6-(2-chloro-4-acetylamino-phenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(I-16)

1.1.5-Methyl-6-(2-chloro-4-amino-phenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine

A mixture of 3 g (8.3 mmol) of5-methyl-6-(2-chloro-4-nitro-phenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(preparation analogously to WO 03/004465), 100 ml of acetic acid, 1 mlof conc. sulfuric acid and 0.5 g of 10% palladium-on-carbon was stirredunder an atmosphere of hydrogen overnight.

The reaction mixture was then filtered off with suction throughkieselguhr, the ethyl acetate phase was diluted with water and theaqueous phase was extracted three times with methylene chloride. Thecombined organic phases were washed with NaHCO₃ solution and water untilneutral and concentrated. The residue was purified by columnchromatography using cyclohexane/ethyl acetate mixture.

This gave 2.1 g (80%) of the title compound 1.1. as a colorless solid.

¹H-NMR (CDCl₃, δ in ppm): 8.45 (s, 1H); 7.0 (d, broad, 1H); 6.9 (s,broad, 1H); 6.7 (d, broad, 1H); 3.6-4.1 (s, very broad, 2H); 3.1 (dd,0.5H); 2.95 (dd, 0.5H); 2.85 (dd, 0.5H); 2.7 (dd, 0.5H); 2.4 (s, 3H),2.1 (m, 1H); 1.0-1.4 (m, 2H); 0.7-0.85 (m, 6H)

1.2.5-Methyl-6-(2-chloro-4-acetylamino-phenyl)-7-(2-methyl-butyl)-1,2,4-triazolo[1,5a]pyrimidine

0.25 g (3 mmol) of pyridine and 0.2 g (2.5 mmol) of acetyl chloride wereadded to a mixture of 0.5 g (1.5 mmol) of5-methyl-6-(2-chloro-4-amino-phenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(example 1.1.) and 10 ml of methylene chloride, and the mixture wasstirred at room temperature for about 1 hour.

The reaction mixture was then washed with dilute hydrochloric acid andwater and concentrated. The residue obtained was 0.5 g (88%) of thetitle compound 1.2.

¹H-NMR (CDCl₃, δ in ppm): 8.45 (s, 1H); 8.15 (s, broad, 1H); 7.95 (s,broad, 1H); 7.65 (m, 1H); 7.2 (m, 1H); 3.1 (dd, 0.5H); 2.95 (dd, 0.5H);2.85 (dd, 0.5H); 2.65 (dd, 0.5H); 2.4 (s, 3H); 2.3 (s, 3H); 2.1 (m, 1H);1.0-1.35 (m, 1H); 0.7-0.85 (m, 6H)

Example 25-Methyl-6-(2,6-difluoro-4-benzylthiophenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(I-3)

Under an atmosphere of nitrogen, 0.3 g (12.5 mmol) of sodium hydridewere added to 1.3 g (10 mmol) of benzyl mercaptan in 50 ml ofN-methylpyrrolidone, and the mixture was stirred at room temperatureuntil the evolution of hydrogen had ceased (about 15 min).

3.3 g (10 mmol) of5-methyl-6-(2,4,6-trifluorophenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(preparation analogously to WO 03/004465) were then added, and themixture was stirred at room temperature for about 2 hours. The reactionmixture was then diluted with water, and the aqueous phase was extractedthree times with methyl t-butyl ether. The combined organic phases werewashed twice with water and concentrated. The residue obtained waspurified by MPLC on silica gel RP-18 using acetonitrile/water mixtures.This gave 2.1 g (50%) of the title compound 2 as a light-yellow, viscousmaterial.

¹H-NMR (CDCl₃, δ in ppm): 8.45 (s, 1H); 7.4 (m, 5H); 6.95 (d, 2H); 4.25(s, 2H); 3.0 (dd, 1H); 2.75 (dd, 1H); 2.45 (s, 3H); 2.05 (m, 1H); 1.25(m, 1H); 1.1 (m, 1H); 0.8 (t, 3H); 0.7 (d, 3H)

Example 35-Methyl-6-(2,6-difluoro-4-benzylsulfoxyl-phenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(I-5)

0.5 g (2.2 mmol) of 77% strength m-chloroperbenzoic acid was added to0.9 g (2 mmol) of5-methyl-6-(2,6-difluoro-4-benzyl-thiophenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(Example 2) in 30 ml of methylene chloride, and the mixture was stirredat room temperature for about 2 hours.

Dilute aqueous sodium hydroxide solution was then added to the reactionmixture, the phases were separated and the organic phase was extractedtwice with water. The organic phase was concentrated and the residue waspurified by MPLC on silica gel RP-18 using acetonitrile/water mixtures.This gave 0.7 g (77%) of the title compound 3 as a light-yellow oil.

¹H-NMR (CDCl₃, δ in ppm): 8.5 (s, 1H); 7.35 (m, 3H); 7.1 (m, 4H); 4.2(dd, 2H); 3.05 (dd, 1H); 2.7 (dd, 1H); 2.45 (s, 3H); 2.1 (m, 1H); 1.3(m, 1H); 1.1 (m, 1H); 0.8 (t, 3H); 0.75 (d, broad, 3H)

Example 45-Methyl-6-(2,6-difluoro-4-benzylsulfonyl-phenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(I-6)

0.3 g (1.3 mmol) of 77% strength m-chloroperbenzoic acid was added to0.4 g (1 mmol) of5-methyl-6-(2,6-difluoro-4-benzyl-sulfoxylphenyl)-7-(2-methylbutyl)-1,2,4-triazolo[1,5a]pyrimidine(example 3) in 10 ml of methylene chloride, and the mixture was stirredat room temperature for about 1 hour.

The reaction mixture was then extracted with dilute aqueous sodiumhydroxide solution and concentrated, and the residue was purified bycolumn chromatography using cyclohexane/ethyl acetate mixtures. Thisgave 0.25 g (53%) of the title compound 4 as a light-yellow oil.

¹H-NMR (CDCl₃, δ in ppm): 8.5 (s, 1H); 7.35 (m, 5H); 7.2 (d, 2H); 4.45(s, 2H); 3.0 (dd, 1H); 2.7 (dd, 1H); 2.4 (s, 3H); 2.1 (m, 1H); 1.3 (m,1H); 1.1 (m, 1H); 0.8 (t, 3H); 0.7 (d, 3H) I

Table of active compounds Physical data No. R¹ R² R_(n) X (m.p. [° C.],IR [cm⁻¹], ¹H-NMR [ppm]) I-1 but-3-enyl methyl 2,6-F₂ 4-S-t-C₄H₉ 100-102I-2 but-3-enyl methyl 2,6-F₂ 4-SO₂-t-C₄H₉ 17614 178 I-3 2-methylbutylmethyl 2,6-F₂ 4-S-benzyl 8.45 (s, 1H); 4.25 (s, 2H); 2.45 (s, 3H) I-42-methylbutyl methyl 2,6-F₂ 4-S-t-C₄H₉ 95-97 I-5 2-methylbutyl methyl2,6-F₂ 4-SO-benzyl 8.5 (s, 1H); 4.2 (dd, 2H); 2.45 (s, 3H) I-62-methylbutyl methyl 2,6-F₂ 4-SO₂-benzyl 8.5 (s, 1H); 4.45 (s, 2H); 2.4(s, 3H) I-7 2-methylbutyl methyl 2,6-F₂ 4-S—CH₃ 8.45 (s, 1H); 2.6 (s,3H); 2.45 (s, 3H) I-8 2-methylbutyl methyl 2,6-F₂ 4-SO—CH₃ 8.5 (s, 1H);2.85 (s, 3H); 2.45 (s, 3H) I-9 2-methylbutyl methyl 2,6-F₂ 4-SO₂—CH₃ 8.5(s, 1H); 3.25 (s, 3H); 2.5 (s, 3H) I-10 2-methylbutyl methyl 2,6-F₂4-SO₂-n-C₃H₇ 8.45 (s, 1H); 3.2 (t, 2H); 2.45 (s, 3H) I-11 2-methylbutylmethyl 2,6-F₂ 4-S—C₂H₅ 8.45 (s, 1H); 3.1 (q, 2H); 2.45 (s, 3H) I-122-methylbutyl methyl 2,6-F₂ 4-S-n-C₃H₇ 8.45 (s, 1H); 3.0 (t, 2H); 2.45(s, 3H) I-13 2-methylbutyl methyl 2,6-F₂ 4-SO—C₂H₅ 8.45 (s, 1H); 7.4 (m,2H); 2.45 (s, 3H) I-14 2-methylbutyl methyl 2,6-F₂ 4-SO₂—C₂H₅ 122-124I-15 2-methylbutyl methyl 2,6-F₂ 4-SO-n-C₃H₇ 8.5 (s, 1H); 2.9 (t, 2H);2.45 (s, 3H) I-16 2-methylbutyl methyl 2-Cl 4-NH—CO—CH₃ 8.45 (s, 1H);2.4 (s, 3H); 2.3 (s, 3H)

Examples of the activity against harmful fungi

The fungicidal activity of the compounds of the formula I wasdemonstrated by the following experiments:

The active compounds were formulated separately as a stock solutioncomprising 0.25% by weight of active compound in acetone or DMSO. 1% byweight of the emulsifier Uniperol® EL (wetting agent having emulsifyingand dispersing action based on ethoxylated alkylphenols) was added tothis solution. The stock solutions of the active compounds were dilutedwith water to the stated concentration.

Use Examples Example 1 Activity Against Mildew on Cucumber Leaves Causedby Sphaerotheca fuliginea, Protective Application

Leaves of cucumber seedlings of the cultivar “Chinese Snake” which hadbeen grown in pots were, at the cotyledon stage, sprayed to runoff pointwith an aqueous suspension in the active compound concentrationindicated below. 20 hours after the spray coating had dried on, theplants were inoculated with an aqueous spore suspension of mildew ofcucumbers (Sphaerotheca fuliginea). The plants were then cultivated in agreenhouse at 20-24° C. and 60-80% relative atmospheric humidity for 7days. The extent of the mildew development was then determined visuallyin % infection of the cotyledon area.

In this test, the plants which had been treated with 250 ppm of thecompounds I-7 and I-8 showed an infection of ≦20%, whereas the untreatedcontrol plants were 90% mildew infected.

Example 2 Activity Against Early Blight of Tomato Caused by Alternariasolani

Leaves of potted plants of the cultivar “Golden Princess” were sprayedto runoff point with an aqueous suspension having the concentration ofactive compound stated below. The next day, the leaves were infectedwith an aqueous spore suspension of Alternaria solani in a 2% biomaltsolution having a density of 0.17×10⁶ spores/ml. The plants were thenplaced in a water-vapor-saturated chamber at temperatures between 20 and22° C. After 5 days, the blight on the untreated, but infected controlplants had developed to such an extent that the infection could bedetermined visually in %.

In this test, the plants which had been treated with 250 ppm of thecompounds I-4, I-7, I-12 and I-13 showed an infection of ≦30%, whereasthe untreated (control) plants were 90% damaged by the fungal infection.

Example 3 Activity Against Peronospora of Grape Vines Caused byPlasmopara viticola

Leaves of potted vines were sprayed to runoff point with an aqueoussuspension having the concentration of active compound stated below. Thenext day, the undersides of the leaves were inoculated with an aqueoussporangial suspension of Plasmopara viticola. The vines were initiallyplaced in a water-vapor-saturated chamber at 24° C. for 48 hours andthen in a greenhouse at temperatures between 20 and 30° C. for 5 days.After this period of time, the plants were again placed in a humidchamber for 16 hours to promote sporangiophore eruption. The extent ofthe development of the infection on the undersides of the leaves wasthen determined visually.

In this test, the plants which had been treated with 250 ppm of thecompounds I-4 to I-7 showed an infection of ˜30%, whereas the untreated(control) plants were 80% infected by harmful fungi.

1. A triazolopyrimidine of the formula I

where the index and the substituents are as defined below: R¹ is C₁-C₁₀-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₁₀-cycloalkyl, C₃-C₁₀-cycloalkenyl, phenyl, naphthyl or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which is attached via carbon to the triazolopyrimidine and contains one to four heteroatoms from the group consisting of O, N and S, where R¹ may be partially or fully halogenated or substituted by one to four identical or different groups R^(a): R^(a) is halogen, cyano, nitro, hydroxyl, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkylcarbonyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylthio, C₁-C₆-alkylamino, di-C₁-C₆-alkylamino, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-cycloalkyl, phenyl, naphthyl, a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S, where these aliphatic, alicyclic or aromatic groups for their part may be partially or fully halogenated or carry one to three groups R^(b): R^(b) is halogen, cyano, nitro, hydroxyl, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, alkyl, alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkoxy, alkylthio, alkylamino, dialkylamino, formyl, alkylcarbonyl, alkylsulfonyl, alkylsulfoxyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, where the alkyl groups in these radicals contain 1 to 6 carbon atoms and the abovementioned alkenyl or alkynyl groups in these radicals contain 2 to 8 carbon atoms and the abovementioned groups may be partially or fully halogenated; and/or one to three of the following radicals: cycloalkyl, cycloalkoxy, heterocyclyl, heterocyclyloxy, where the cyclic systems contain 3 to 10 ring members; aryl, aryloxy, arylthio, aryl-C₁-C₆-alkoxy, aryl-C₁-C₆-alkyl, hetaryl, hetaryloxy, hetarylthio, where the aryl radicals preferably contain 6 to 10 ring members and the hetaryl radicals 5 or 6 ring members, where the cyclic systems may be partially or fully halogenated or substituted by alkyl or haloalkyl groups; R² is C₁-C₄-alkyl which may be substituted by halogen, cyano, nitro or C₁-C₂-alkoxy; n is 0 or an integer from 1 to 4; R is halogen, cyano, C₁-C₆-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₁-C₆-haloalkyl, C₂-C₁₀-haloalkenyl, C₁-C₆-alkoxy, C₂-C₁₀-alkenyloxy, C₂-C₁₀-alkynyloxy, C₁-C₆-haloalkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₁-C₈-alkoxycarbonyl, C₂-C₁₀-alkenyloxycarbonyl, C₂-C₁₀-alkynyloxycarbonyl, aminocarbonyl, C₁-C₈-alkylaminocarbonyl, di-(C₁-C₈-)alkylaminocarbonyl, C₁-C₈-alkoximinoalkyl, C₂-C₁₀-alkenyloximinoalkyl, C₂-C₁₀-alkynyloximinoalkyl, C₁-C₈-alkylcarbonyl, C₂-C₁₀-alkenylcarbonyl, C₂-C₁₀-alkynylcarbonyl, C₃-C₆-cycloalkylcarbonyl, or a five- to ten-membered saturated, partially unsaturated or aromatic heterocycle which contains one to four heteroatoms from the group consisting of O, N and S; X is SO_(m)—R^(x), NR^(x)R^(y) or NR^(x)—(C═O)—R^(y); R^(x), R^(y): are: hydrogen, C₁-C₆-alkyl, C₂-C₁₀-alkenyl, C₂-C₁₀-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, where the above radicals may be partially or fully halogenated or substituted by cyano, C₁-C₄-alkoximino, C₂-C₄-alkenyloximino, C₂-C₄-alkynyloximino or C₁-C₄-alkoxy; m is 0 or an integer 1 to
 3. 2. A triazolopyrimidine of the formula I′

where the index and the substituents are as defined below: R¹ is C₃-C₈-alkyl, C₃-C₈-alkenyl, C₃-C₈-alkynyl, C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl; where R¹ may be partially or fully halogenated or substituted by one to four identical or different groups R^(a): R^(a) is halogen, cyano, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkoxy, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkoximino, C₂-C₆-alkenyloximino, C₂-C₆-alkynyloximino, C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl, where the aliphatic or alicyclic groups for their part may be partially or fully halogenated or carry one to three groups R^(b): R^(b) is halogen, cyano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-alkylcarbonyl, C₁-C₆-haloalkylcarbonyl or C₁-C₆-alkoxy; R² is C₁-C₄-alkyl which may be substituted by halogen; n is an integer from 0 to 2; R is fluorine, chlorine, bromine, cyano, C₁-C₆-alkyl, C₁-C₆-alkoxy; X is SO—R^(x), SO₂—R^(x) or NR^(x)—(C═O)—R^(y); R^(x), R^(Y) are: hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl or C₃-C₆-cycloalkyl, where the above radicals may be partially or fully halogenated.
 3. A process for preparing compounds of the formula I as claimed in claim 1 or 2 which comprises reacting 5-aminotriazole of the formula II

with dicarbonyl compounds of the formula III

where the substituents R, X, R¹ and R² and the index n are as defined in claim
 1. 4. A dicarbonyl compound of the formula III, which is defined in claim
 3. 5. A composition suitable for controlling harmful fungi, comprising a solid or liquid carrier and a compound of the formula I as claimed in claim
 1. 6. The use of the compounds I as claimed in claim 1 for preparing a composition suitable for controlling harmful fungi.
 7. A method for controlling harmful fungi, which comprises treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of a compound of the formula I as claimed in claim
 1. 